134241-95-5

Upstream product

• 186581-53-3 diazomethane 
• 37051-56-2 5-Oxo-2-cyclohexenecarboxylic acid 

Downstream Products

• 134224-26-3 (1R,5R)-5-Hydroxy-5-trimethylsilanylethynyl-cyclohex-2-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Processes for producing doxorubicin, daunomycinone, and derivatives of doxorubicin

Daunomycinone is a known precursor of the well known antibiotic and antineoplastic, doxorubicin. Daunomycinone may be synthesized by preparing mono ketal of a 1,4-naphthoquinone as the precursor of the CD rings of daunomycinone followed by preparing a pre

Processes for producing doxorubicin, daunomycinone, and derivatives of doxorubicin

To produce doxorubicin and its analogues methyl 3alpha, 5alpha-dihydroxy-5beta-(trimethylsilylethynyl)-2alpha-nitromethylcyclohexane-1beta-carboxylate acetonide is condensed with 1,4-dihydro-4,4,5-trimethoxy-1-oxonaphthalene in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene in an aprotic solvent to produce 3-[ (2beta-carbomethoxy-4beta-ethynyl-4alpha, 6alpha-(di-O-isopropylidenyl)cyclohexanyl-1-yl]-nitromethyl-4,4,5-trimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene; which is cyclized to produce 9beta-ethynyl-12-hydroxy-7alpha,9alpha-(di-O-isopropylidenyl)-6-nitro-4,5,5-trimethoxy-5,5a,6,6a,7,8,9,10,10a,11-decahydro -11-naphthacenone. The decahydro-11-naphthacenone is converted to 7alpha-9alpha,(di-O-isopropyl-idenyl)-4,5-dimethoxy-9beta-ethynyl-12-hydroxy-6-nitro-6,6a,7,8,9,10,10a,11-octahydro-11, -naphthacenone. The octahydro-11-naphthacenone is oxidized to 7alpha-9alpha, (di-O-isopropyl-idenyl)-9beta-ethynyl-11-hydroxy-4-methoxy-6-nitro-7,8,9,10,-tetrahydro-5,12-naphthacenedione which is converted to 6-desoxy-6-nitrodaunomycinone, daunomycinone and related 6-substituted analogues of daunomycinone.

Processes for producing doxorubicin, daunomycinone, and derivatives of doxorubicin

To produce doxorubicin and its analogues, methyl 3alpha, 5alpha-dihydroxy-5beta-(trimethylsilylethynyl)-2alpha-nitromethylcyclohexane-1beta-carboxylate acetonide is condensed with 1,4-dihydro-4,4,5-trimethoxy-1-oxonaphthalene in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene in an aprotic solvent to produce 3-[(2beta-carbomethoxy-4beta-ethynyl-4alpha, 6alpha-(di-0-isopropylidenyl)cyclohexanyl-1-yl]-nitromethyl-4,4,5-trimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene, which is cyclized to produce 9beta-ethynyl-12-hydroxy-7alpha,9alpha-(di-0-isopropylidenyl)-6-nitro-4,5,5-trimethoxy-5,5a,6,6a,7,8,9,10,10a,11-decahydro-11-naphthacenone. The decahydro-11-naphthacenone is converted to 7alpha-9alpha,(di-0-isopropylidenyl)-4,5-dimethoxy-9beta-ethynyl-12-hydroxy-6-nitro-6,6a,7,8,9,10,10a,11-octahydro-11,-naphthacenone. The octahydro-11-naphthacenone is oxidized to 7alpha-9alpha, (di-0-isopropylidenyl)-9beta-ethynyl-11-hydroxy-4-methoxy-6-nitro-7,8,9,10,-tetrahydro-5,12-naphthacenedione which is converted to 6-desoxy-6-nitrodaunomycinone, daunomycinone and related 6-substituted analogues of daunomycinone.

Synthesis of a ring a precursor of doxorubicin: Stereoselective control of the epoxidation of a homoallylic alcohol by hydroxyl and ester groups

The key step in a synthesis of a precursor for ring A in doxorubicin is the stereoselective control of the epoxidation of a homoallylic alcohol by ester and hydroxyl groups; the result leads to a new method of forming lactones in excellent yields under ne